2,1,3-benzothiadiazole dimers: Preparation, structure, and transannular electronic interactions of syn-and anti-[2.2](4,7)benzothiadiazolophanes

Abstract

The cyclophanes comprised of two 2,1,3-benzothiadiazole (BTD) rings, anti-and syn-[2.2](4,7)benzothiadiazolophanes (anti-1 and syn-1), were prepared for the first time. The differences of the physical properties in the overlapping mode of the π-systems are clearly observed, and syn-1 shows much more significant transannular π-electronic interactions than anti-1 especially in the redox properties and the stability of the radical anion species. © 2010 The Chemical Society of Japan.